In recent years, researchers have devoted much discussion to finding ways to increase the academic success of Black males in K-12 and higher education. Despite this emphasis, Black male enrollment in higher education stands at 4.5%, which is the same as it was in 1976. One factor noted by researchers for the stagnation among Black male college enrollment is their disproportionate departure from high school. Therefore, this qualitative study of college-bound high school seniors discusses four critical factors that contribute to Black males premature departure from high school. Implications for practice and future research are discussed.